I was visiting Orchard Road yesterday on a Sunday & I didn't enjoy the visit. It was packed everywhere & I didn't even find what I was looking for:(
Wanted to have lunch there but with the all the crowds & high prices at the food court I decided to eat at the kopitiam close to my home.
Living close to Orchard Rd can be convenient but I for me visiting JB is more value. If I was living in Woodlands I could make more visits to JB. So it depends on your life style & income.